Re: Funding the sailing lifestyle
Where you live has an impact on making the lifestyle work. Living on the coast, or at least one of the great lakes, is essential. Also, you need to be able to work with your hands and have some working knowledge of how to work on boats (fiberglass, mechanical, electrical, etc.) If you have these two things covered and already have a boat of your own that is paid for and you can live on, then you can make it happen. However, starting out, you won't be sailing off to the Carribean, you'll be living aboard, most likely on the hook, and working at a marina; boatyard preferably, while you make your boat seaworthy (any repairs, good sail inventory, good nav. equip., etc.). If you live near a major boating area, such as Annapolis, MD, Charleston, SC, or basically anywhere in Florida, that's a plus because most boatyards will start you out at $15-$17/hr. minimum.
If you don't know how to work on boats, many yards will train you but then you will make less money. Also, if you are not happy with the boat you have, being in a yard, you will be suprised how many deals come your way. You may end up being able to upgrade after saving some money.
This is one plan for being able to move aboard your boat.
I also know other people that travel from place to place and secure work in each new place they come to. This, again, is much easier to do if you are able to work on boats. You can arrive, drop the hook, and usually find work at one of the yards if it is a decent size city.
You will have to live on a budget, probably be on the hook, not in a slip, to start off with, and will need to save money. Then you can work 6 to 9 months a year and take the other 3 off to go sailing if you have saved your money and lived frugally. Most yards are used to employees that do this sort of thing.
You really don't need that much money. If you anchor out, use solar or wind power, actually sail instead of motoring....then you are left with boat insurance and yearly registration, which is not that much on a boat your size, and the cost of groceries.
We live on our boat and travel from place to place. Right now we are on the East Coast. It took my husband 4 days after we arrived here to find a job at a yard. He plans to work there until the end of summer and then we will head South for the winter and he will pick up some part time work in Florida at a yard. We anchor out most of the time, buy groceries and cook on board, sail instead of motor, even if that means waiting for the winds to cooperate, we have no need for a car so no expenses there, and we use solar power. We've never been "broke", although things have been tight at times. It just depends on what you are willing to sacrifice to make your dream a reality. Our first year was rough but since then, we've managed to save enough each year to spend a month in the Bahamas.
Just some ideas to think about......I don't know if what works for us would for you but you'll never know unless you try! I wish you the best whatever you decide to do! Good Luck!